Questions tagged [inductive-effect]
Use for questions regarding the so called inductive effect of substituents on properties of compounds.
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-R and -I power at different positions in an organic compound [closed]
Why is the -R and -I power of a group minimum at para position whereas it is maximum at ortho position.
For eg: In nitro benzyl carbocation, if nitro(acting as a -I as well as a -R group) is present ...
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1answer
34 views
How to explain regioselectivity in nucleophilic aromatic substitution
I’m trying to rationalise the major regioisomeric product of the following reaction of an arylchloride in the presence of sodium amide:
I have predicted that the para-substituted product is formed as ...
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1answer
40 views
Order of −I effect among ethenyl and 1-propenyl groups
We know that both ethenyl $\ce{-CH=CH}_2$ and 1-propenyl $\ce{-CH=CH-CH3}$ are electron-withdrawing groups when attached to hydrocarbon chain. Which one has greater electron withdrawing power?
The $\...
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1answer
45 views
Inductive effect vs electronegativity [closed]
Why is the inductive effect of chlorine, bromine, and iodine stronger than that of hydroxy group, even though oxygen is more electronegative?
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1answer
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Does the benzene ring in styrene show a negative inductive effect on the ethenyl group?
I know that a group exerts an inductive effect on another one if there is a difference in electronegativity. In the case of styrene (1) all the atoms are sp2-hybridized. So, how could the phenyl ring ...
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95 views
Estimation of dipole moments in aromatic compounds
If it asks to compare dipole moment in aromatic compounds then do we see inductive or resonance effects or do we see a mix of both?
E.g. we have to compare dipole moment in pyrrole and furan then in ...
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1answer
320 views
Comparing reactivity of 1-chloroethane and 1-chloropropane in an SN1 reaction
Beginning with a reference to a well known question.
Order by reactivity towards SN1 reaction.
According to some facts about SN1 reactions, rate depends on:
Stability of carbocations
Better leaving ...
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53 views
Inductive effect of acetyl group
Question:
Since the acetyl group provides $-M$, methyl $+I$ and chlorine $-I$, it is obvious that the correct order is as given in option $(a)$
However while solving such questions I would compare ...
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Does the electron displacement effect act only on sigma electrons?
Our teacher told us that the inductive effect or the electron displacement effect can only affect the sigma electrons. I did not understand why this should be.
I reasoned it can not affect the pi ...
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1answer
216 views
Carbanion Stability order [duplicate]
Why is a 3° Carbanion unstable than 1° Carbanion? Carbon atom with negative charge will become little electropositive relative to a neutral carbon. So if a Carbanion is attached to three neutral ...
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1answer
99 views
The most acidic hydrogen among ethane, ethene, ethyne and allene
Among
$$\ce{CH3-CH3}\qquad\ce{CH2=CH2}\qquad\ce{HC≡CH}\qquad\ce{CH2=C=CH2}$$
I need to find out the one having highest acidic hydrogen.
As per my observations, there are two equivalent resonating ...
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1answer
529 views
Ortho-para directing and meta directing groups: Activating or deactivating the aromatic ring?
Determine the reactivity of the above compounds (activating or deactivating; ortho-para or meta directing). Explain your answers. You may use resonance structures in your explanation. Which molecule ...
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2answers
616 views
Does Cl- Have more -I effect or +M effect ( Resonance effect)?
In this question my answer was (A) because i though $\ce{NH2}$ group would give more electrons than $\ce{Cl-}$ . But the correct answer is (D) and my teacher's reason is that chlorine has more ...
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1answer
55 views
Inductive effect of -NHMe
Why does $\ce{-NHMe}$ show -I effect. I think it should be opposite. I know that $\ce{-Me}$ groups are electron donating in nature. So the nitrogen atom will have a small $\delta^-$ charge. So then ...
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Methyl group and acidic nature [duplicate]
After reading various answers here on StackExchange (like Why is the methyl group electron-donating via the inductive effect? and Strongest negative inductive effect group between trimethylammonium, ...
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1answer
242 views
Why is formic acid stronger than acetic acid [duplicate]
Even when acetate ion is stabilized due to resonance why is it a weaker acid than formic acid. It is true that acetic acid has +I effect due to methyl group present on it but resonance is a stronger ...
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Problem in defining the Inductive effect
Inductive effect is introduced in many textbooks by giving an example of an alkyl halide $R-X$.
The bond C1-X is polar due to electronegativity difference, therefore X gains partial negative charge ∆(-...
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1answer
161 views
Stability of carbocation directly attached to a halogen atom [duplicate]
I have two compounds..
How is the first one more stable?
As I have been taught that -I effect of Chlorine dominates its +R effect but to explain this case, My teacher is saying that because of the ...
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1answer
60 views
Para effects on substituents in aromatic compounds
I wanted to know how to compare the following compounds on basis of acidic strength.
I have to find the acidic strength of following compounds with $\mathrm{X}=\ce{CH3, \ OCH3,}$ and $\ce{NO2}$.
For ...
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202 views
Comparison of basicity of Aniline, p-Anisidine, and o-Anisidine [duplicate]
I have a question where I am required to compare the basicity of Aniline, o-Anisidine, and p-Anisidine.
Now here's what I do know:-
In ortho substituted aniline, an ortho effect acts which reduces ...
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0answers
22 views
Comparison between groups with -I effects
So I have a few questions in my book that require me to compare between two different groups on the basis of their -I effects. I have a few questions on this that have been bugging me for quite a ...
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1answer
720 views
Effect of phenyl and vinyl substituents on Acidity of carboxylic
Recently I came across this statement in my textbook:
Direct attachment of groups such as phenyl or vinyl to the carboxylic
acid, increases the acidity of corresponding carboxylic acid contrary
...
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3answers
122 views
Odd looking carbocation stability order [duplicate]
I am studying introductory organic chemistry, suddenly this one started looking odd,
The carbocation stability for three compounds as given by my book is shown below,
Let me call those as ...
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1answer
137 views
Change in inductive effect of a susbstituent when -R group replaces -H atom
There are several examples where the negative inductive effect of a substituent gets increased when a hydrogen atom on that substituent is replaced by an alkyl group.
Some particular examples:
$$\ce{...
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Trimethylsilyl vs tert-butyl as activating substituent of benzene
Would trimethylsilane as a benzene substituent have an activating effect relative to tert-butyl for electrophilic substitution reactions?
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1answer
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Why O and N promote SN1 but C=O inhibit SN1 although both are electron-withdrawing?
Source:
Jonathan Clayden, Nick Greeves, Stuart Warren, Organic Chemistry 2th Edition, 339.
The general idea I got so far, is that, carbocation will be more stable if the + charge at central C is ...
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0answers
114 views
How does the relative acidity of 2,3-dinitrophenol compare to that of 2,4-dinitrophenol?
I am assuming that the -I inductive effect in 2,3-dinitrophenol is stronger than in 2,4-dinitrophenol since it operates through less bonds, therefore on inductive grounds it should have a lower $\...
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1answer
162 views
What is the stability order of the carbocation and carboanion?
So I came up with examples as below:
1
2
Now I am confused about the +I and -I effect in these structures since to my knowledge it can only be applied when there is a substituent (I might be wrong)...
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0answers
154 views
Which substitutent should be placed on axial position in SCl2(OCH3)2?
According to Bent's rule, in $\mathrm{sp^3d}$ more electronegative element is placed on the axial position, so between $\ce{Cl}$ and $\ce{OCH3}$ in $\ce{SCl2(OCH3)2}$ which should be placed on axial ...
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0answers
44 views
Does an electronegative atom which carries a negative formal charge withdraw electrons by induction?
Electronegative atoms withdraw electrons by their inductuve effect. Does this fact remain true even when they are heavily loaded with electrons through negative formal charge? Are these two ideas ...
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1answer
113 views
Inductive effect of alkyl ammonium groups
Why $\ce{-NR3+}$ has more -I effect than $\ce{-NH3+}?$
And what about order of $\ce{-NHR2+}$ and $\ce{-NH2R+}?$
My attempts
I got idea about electronegativity of carbon atom in $\ce{R}$ is more than ...
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674 views
Which of the following groups show +M and -I effect?
Which of the following group show +M and -I effect?
(A) $\ce{-\underset{\underset{\huge O}{||}}{C}-F}$
(B) $\ce{-\underset{\underset{\huge O}{||}}{C}-OR}$
(C) $\ce{-O^-}$
(D) $\ce{-OH}$
Answer is ...
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2answers
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When 2-pentene reacts with HBr, what will be the major product?
If we consider the first step (formation of carbocation by the attack of the proton).
A couple of textbooks I referred say that when the substituents on the $\ce{C=C}$ are different, the direction of ...
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1answer
156 views
Confusions about inductive effect and acid strength
If one of the hydrogens in the alkyl side chain of ethanoic acid is replaced with an atom of Chlorine, the acid has a larger Ka value. My book says this is since the Cl "borrows" electron density from ...
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1answer
216 views
Which of the two structures is more stable?
Which of the two structures is more stable?
As far as I know, alkenes with a greater number of hyperconjugating structures are more stable. Hyperconjugation has a greater stabilizing effect than ...
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1answer
243 views
Does hyperconjugation into sigma-star explain methylamine's increased basicity relative to ammonia?
The inductive effect with the polarisation of the C-N bond obviously plays a role in stabilising the positive charge of the conjugate acid. But given the similar electronegativities for C and H, CH3 ...
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1answer
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Which Carbocation is most stable among the three? [closed]
According to me the answer should be (C) as that Carbocation will be stablized by resonance with Chlorine.
I have read that resonance is the biggest deciding factor about the stability of a ...
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978 views
Why is C2H5 a stronger +I group than CH3?
While reading about the basic character of amines, I came across a note which said that $\ce{CH3-CH2-NH2}$ was more stable than $\ce{CH3-NH2}$ as $\ce{C2H5}$ was a stronger +I group than $\ce{CH3}$.
...
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1answer
921 views
Stability order of methy benzyl cations?
I know that meta position shown no resonance effect and hyperconjugation effect . So According to the order given I guess Hyperconjugating effect is taken into account as -CH3 has no Resonance effects....
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1answer
429 views
Give the order of nucleophilic addition reaction in the following -
I am confused that whether we should take only inductive or hyperconjugation effect also into consideration while finding the order. As the answer in the book is only according to inductive effect . ...
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Mechanism of substitution for disubstituted benzene
Here, I count the individual effects of the two oppositely directing groups. I assume that the deactivation of $\ce{NO_2}$ group at ortho and meta positions is higher. While bromination, I get the ...
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1answer
1k views
Comparing relative negative inductive effect of substituents (dialkyl amine, amine, alkoxide, fluoride)
Which of the following is correct with respect to the negative inductive effect of the substituents?
1. $\ce{-NR2 < -OR < -F}$
2. $\ce{-NH2 < -OR < -F}$
3. $\ce{-NR2 > -OR > -F}...
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2answers
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Inductive effect of hydrogen isotopes
Why does the electron-donating inductive effect (+I) of the isotopes of hydrogen decrease in the order $\ce{T} > \ce{D} > \ce{H}$?
(where T is Tritium and D is Deuterium)
Google has nothing to ...
